As The New York Times describes, Gillum is an “avatar” for the corruption of Tallahassee city government.

A new report details just a few of the corruption scandals that continue to surround Florida Democrat gubernatorial nominee Andrew Gillum.

As The New York Times describes, Gillum is an “avatar” for the corruption of Tallahassee city government. Throughout his time as Mayor, Gillum’s cozy relationships with lobbyists and the “blurring lines” between his personal interests and the public’s have placed him at the center of an FBI corruption probe, as well as a state ethics commission investigation.

Andrew Gillum’s entire political career has been tainted by corruption. Floridians can’t trust him.

Yet an examination of Mr. Gillum’s record lays bare the central contradiction of his political life: Self-styled as an activist-minded populist, with a lunch-pail upbringing in south Miami-Dade County, he is also an avatar of the capital city he runs — a town powered by ambition, horse-trading and alliances with well-placed power players.

One top campaign adviser — Sean Pittman, a close friend and mentor whom Mr. Gillum met as a student at Florida A&M — is also one of the city’s subcontracted lobbyists. Another senior strategist, Sharon Lettman-Hicks, also a confidante since college, paid the mayor a salary of $71,680 in 2017 to advise her boutique public-relations consulting firm, though he spent virtually all of his non-mayoral time running for governor. Until recently, Ms. Lettman-Hicks also served as the landlord of his campaign headquarters, collecting $38,087.50 in rent from March 2017 through August of this year, according to campaign finance records.

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‘Does he have friends who are lobbyists? You bet,’ said Allan Katz, a former city commissioner who served with Mr. Gillum and later became Mr. Obama’s ambassador to Portugal.

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And as Mr. Gillum seeks the state’s highest post, at least one of those friends has brought baggage, dragging his name into an F.B.I. investigation and, unbeknown to him, placing him in the extended company of undercover agents. About two years ago, a lobbyist, Adam Corey, who had been close with Mr. Gillum since their student government days, introduced him to men who identified themselves as out-of-town developers eager to invest in property on Tallahassee’s south side — but were in fact working undercover to investigate the city’s community redevelopment agency for possible corruption.

Mr. Gillum has insisted that investigators told him he is not their target, and the inquiry has yet to produce any indictments. But subpoenaed documents revealed that Mr. Gillum took two personal trips in 2016 with Mr. Corey: one to Costa Rica with a top Gillum adviser, Mr. Pittman, and another to New York with Mr. Gillum’s younger brother and the agents. Mr. Gillum has said he paid his own way for most of the travel, with his brother treating him to a Broadway performance of ‘Hamilton’ and a hotel stay. Both trips are under investigation by Florida’s state ethics commission. Mr. Gillum’s younger brother, Marcus, declined to comment, and a lawyer for Mr. Corey declined to provide further case details.

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At times, though, Mr. Gillum has stood accused of blurring lines that others assumed were clear.

His office spent about $5,000 in taxpayer dollars in 2016 to buy software from a Democratic Party vendor to send political emails, an improper purchase that Mr. Gillum defended until being forced last year to pay the city back and apologize.

He voted in 2013 to give Mr. Corey, his college friend-turned-lobbyist, over $2 million in public funds to redevelop an old power plant into a high-end restaurant, after a city attorney ruled that having the mayor vote on a contract for Mr. Corey, his former campaign treasurer, did not constitute a conflict of interest.

And Mr. Gillum signed off last month on extending a contract for the city’s legislative lobbyist, who retains Mr. Pittman, the top campaign adviser, as a subcontracted lobbyist. Mr. Gillum said Mr. Pittman had not spoken to him about the extension.

Mr. Pittman also joined Mr. Gillum and Mr. Corey on the 2016 trip to Costa Rica that is now under state ethics investigation. (Mr. Pittman was an early investor in Mr. Corey’s restaurant.) Mr. Gillum — who earned $79,176 as mayor last year, in addition to his more than $71,000 in consulting income — has said he and his wife paid for their share of a $1,400-a-night villa in cash; as evidence to ethics investigators, he provided a bank statement showing a $400 withdrawal before their departure. (An attorney for Mr. Corey, who won the villa at a charity auction, said his client was not reimbursed.)